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Sigma-Aldrich

Trimethylsilyl trifluoromethanesulfonate

Trimethylsilyl trifluoromethanesulfonate
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99%

Sinonimo/i:

TMS triflate, TMSOTf, Trifluoromethanesulfonic acid trimethylsilylester

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10 G
44,10 €
50 G
143,00 €
250 G
397,00 €

44,10 €


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Cambia visualizzazione
10 G
44,10 €
50 G
143,00 €
250 G
397,00 €

About This Item

Formula condensata:
CF3SO3Si(CH3)3
Numero CAS:
Peso molecolare:
222.26
Beilstein:
1868911
Numero CE:
Numero MDL:
Codice UNSPSC:
12352103
ID PubChem:
NACRES:
NA.22

44,10 €


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Livello qualitativo

Saggio

99%

Stato

liquid

Indice di rifrazione

n20/D 1.36 (lit.)

P. ebollizione

77 °C/80 mmHg (lit.)

Densità

1.228 g/mL at 25 °C (lit.)

Gruppo funzionale

fluoro
triflate

Stringa SMILE

C[Si](C)(C)OS(=O)(=O)C(F)(F)F

InChI

1S/C4H9F3O3SSi/c1-12(2,3)10-11(8,9)4(5,6)7/h1-3H3
FTVLMFQEYACZNP-UHFFFAOYSA-N

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Applicazioni

Trimethylsilyl trifluoromethanesulfonate has been used in combination with boron trifluoride etherate for the copper-catalyzed asymmetric allylic alkylation (AAA) of allyl bromides, chlorides, and ethers with organolithium reagents in the presence of a chiral ligand.[1][2]
It can be used:
  • As a silylating agent for the synthesis of trimethylsilyl-enol ethers from esters of α-diazoacetoacetic acid.[3]
  • To activate benzyl and allyl ethers for the alkylation of sulfides.[4]
  • To facilitate the conversion of Diels-Alder adducts of Danishefsky′s diene to cyclohexenones without the formation of methoxy ketone by-product.[5]
  • To prepare difluoroboron triflate etherate, a powerful Lewis acid especially in acetonitrile solvent.[6]
  • As a reagent in a Dieckmann-like cyclization of ester-imides and diesters.[7]

It may also be used to catalyze:
  • Acylation of alcohols with acid anhydrides.[8]
  • Reductive coupling of carbonyl compounds with trialkylsilanes to form symmetrical ethers.[9]
  • Glycosidation of 4-demethoxydaunomycinones with 1-O-acyl-L-daunosamine derivatives.[10]

Accessorio

N° Catalogo
Descrizione
Determinazione del prezzo

Pittogrammi

FlameCorrosion

Avvertenze

Danger

Indicazioni di pericolo

Classi di pericolo

Flam. Liq. 3 - Skin Corr. 1B

Rischi supp

Codice della classe di stoccaggio

3 - Flammable liquids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

77.0 °F - closed cup

Punto d’infiammabilità (°C)

25 °C - closed cup

Dispositivi di protezione individuale

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter


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Certificati d'analisi (COA)

Lot/Batch Number

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I clienti hanno visto anche

Slide 1 of 2

1 of 2

BF 3? OEt 2 and TMSOTf: A synergistic combination of Lewis acids.
Myers EL, et al.
Chemical Communications (Cambridge, England), 42, 4434-4436 (2006)
A simple method of preparing trimethylsilyl-and tert-butyldimethylsilyl-enol ethers of ?-diazoacetoacetates and their use in the synthesis of a chiral precursor to thienamycin analogs.
Ueda Y, et al.
Canadian Journal of Chemistry, 62(12), 2936-2940 (1984)
Thomas R Hoye et al.
Organic letters, 8(23), 5191-5194 (2006-11-03)
[Structure: see text] Trialkylsilyl triflates effect cyclization of ester-imides such as 2 to produce adducts such as 4a. Trapping of the in situ generated, nucleophilic ketene acetal (cf. 5a) is a key aspect of the transformation. A range of substrates
Novel glycosidation of 4-demethoxyanthracyclinones by the use of trimethylsilyl triflate. Syntheses of optically active 4-demethoxydaunorubicin and 4-demethoxyadriamycin.
Kimura Y, et al.
Bulletin of the Chemical Society of Japan, 59(2), 423-431 (1986)
Method for sulfide S-benzylation or S-allylation using trimethylsilyl triflate activated benzyl or allyl ethers.
Vedejs E & Eustache J.
The Journal of Organic Chemistry, 46(16), 3353-3354 (1981)

Domande

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  1. How can I determine the shelf life / expiration / retest date of this product?

    1 risposta
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

      Utile?

  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 risposta
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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